Rigorous thinking is asking critical questions about tactics, and having a systematic way of making decisions.
Counterintuitively, rigorous thinking saves you time. Instead of jumping to execute the first idea you think of, you run through basic considerations to stress test your own logic. This, in turn, means less time wasted on fixing easily avoidable mistakes, and more time spent on ideas worth pursuing.
In this way, rigorous thinking acts as a force multiplier and fosters a spirit of entrepreneurialism and ownership among your team. It’s lonely and stressful to be the only one thinking about what to do, looking around the corner to anticipate what’s next.
Let's say you manage 4-5 direct reports. In a culture where rigorous thinking is expected, the idea is this: Any idea goes, but each team member should be prepared to advocate for their idea and defend it. You should be prepared to walk through the upside, downside, data points rooted in reality, and how it works given your assets and constraints. Anyone can ask questions and probe, and these questions are received with gratitude and openness.
The opposite of rigorous thinking is lazy thinking. Lazy thinking is making assumptions you don't even know are assumptions. It's having a black box of logic where "suddenly it works and we have thousands of customers."
✅ Rigorous thinking: "Hey boss, I recommend we do ___. It's likely to work and is worth the time and budget because ___. The downside and potential risks are ___. But we can minimize the risk with a small experiment by doing ___.” In this world, you rarely say no to an idea, because it's not about saying yes or no. It's about vetting an idea. You ask strategic questions, so your employee ends up realizing themselves that the idea won't work in its current iteration.
How to create a culture of rigorous thinking
1. Rigorous thinking starts at the top.
If you set a high bar and celebrate thoughtful decision-making, you send a signal that rigor matters. You don’t let your team get away with lazy assumptions, subpar work, or latch onto surface-level conclusions that don’t capture an accurate picture of the underlying truth.
You may need to model for your team what healthy debate looks like. Mainly, this means leading by example because culture is basically people looking around to see what things are like around here. Your team members pick up on unspoken rules.
For write-ups about the company strategy, it was the same: everyone in the company was encouraged to add comments, ask questions, and challenge assumptions directly in a doc where everyone else could see comments.
3. Create psychological safety
If you want to encourage sparring and healthy debates, you need a foundation of psychological safety. Your team has to trust that you care, and trust that you're asking hard questions because it's better for them, the team, and the idea itself. No one is trying to make anyone look bad or feel stupid.
If you only say yes or no to ideas, your team will keep coming back to you with a similar level of ideas. They won’t know why a strategic proposal worked or didn’t. If you want something to change, it’s your responsibility to invest the time to share your thought process, give feedback, and coach them on how to think differently.
It’s hard, if not near impossible, to learn how to think strategically by reading a book. Understanding a concept in theory is not the same as understanding it in practice. This is why managers must make the time to engage in conversation with their direct reports. Not just conversation about status updates and project management—but deeper conversations about upcoming decisions, challenges your team is facing, and detailed feedback on work output. This is how you unlock the power of hands on, on-the-job learning.
Let's be honest: We managers love sharing our brilliant ideas with a captive audience. It takes self-restraint and hyper-vigilance on our part to stop and let our direct reports talk.
This reminds me of two things: People can only remember so much in one sitting. They will remember more if they’re actively speaking, not only listening.
Rigorous thinking is realizing that 90% of ideas are probably not worth doing, and the ones that are worth doing, won’t just magically work. It’s realizing that many ideas are decent, but decent doesn’t meet the bar for moving forward when you have limited resources (and resources are always limited, even at large organizations).
Rigorous thinking might be conflated with intense processes, long write-ups, and filling out documentation, but I see the two as different. Personally, I hate overkill processes that snuff out creativity and make the lift so high to share an idea that you want to skip sharing it altogether. That's why I love how you can do rigorous thinking while staying nimble and doing the least amount of process possible.
Glasp is a social web highlighter that people can highlight and organize quotes and thoughts from the web, and access other like-minded people’s learning.